DE2040151B2 - Homogeneous, aqueous 4-tert-butylcatechnine solution - Google Patents

Homogeneous, aqueous 4-tert-butylcatechnine solution

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Publication number
DE2040151B2
DE2040151B2 DE2040151A DE2040151A DE2040151B2 DE 2040151 B2 DE2040151 B2 DE 2040151B2 DE 2040151 A DE2040151 A DE 2040151A DE 2040151 A DE2040151 A DE 2040151A DE 2040151 B2 DE2040151 B2 DE 2040151B2
Authority
DE
Germany
Prior art keywords
tert
percent
weight
solution
butylpyrocatechol
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
DE2040151A
Other languages
German (de)
Other versions
DE2040151C3 (en
DE2040151A1 (en
Inventor
Nobuo Ichihara Fuzinami
Tetsuya Chiba Harada
Koichi Chiba Hasegawa
Akira Ichihara Shibatani
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
JSR Corp
Original Assignee
Japan Synthetic Rubber Co Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Japan Synthetic Rubber Co Ltd filed Critical Japan Synthetic Rubber Co Ltd
Publication of DE2040151A1 publication Critical patent/DE2040151A1/en
Publication of DE2040151B2 publication Critical patent/DE2040151B2/en
Application granted granted Critical
Publication of DE2040151C3 publication Critical patent/DE2040151C3/en
Expired legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C39/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring
    • C07C39/02—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring monocyclic with no unsaturation outside the aromatic ring
    • C07C39/08—Dihydroxy benzenes; Alkylated derivatives thereof
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K15/00—Anti-oxidant compositions; Compositions inhibiting chemical change
    • C09K15/04—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds
    • C09K15/06—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds containing oxygen
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S585/00—Chemistry of hydrocarbon compounds
    • Y10S585/949—Miscellaneous considerations
    • Y10S585/952—Reaction stopping or retarding

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Anti-Oxidant Or Stabilizer Compositions (AREA)
  • Polymerisation Methods In General (AREA)
  • Lubricants (AREA)

Description

1515th

Die Erfindung betrifft homogene, wäßrige 4-tert.-Butylbrenzcatechinlösungen mit niedrigem Gefrierpunkt.The invention relates to homogeneous, aqueous 4-tert-butylpyrocatechol solutions with a low freezing point.

4-tert.-Butyibrenzcatechin wird als Polymerisationsinhibitor für zahlreiche Monomere und als Antioxy- dationsmittel für Polyolefine, verschiedene Kunststoffe, Schmiermittel u. dgl. verwendet. Obwohl 4-tert.-Butylbrenzcatechin in Pulverform verwendet werden kann, wird es wegen der leichteren Handhabung häufig in Form einer wäßrigen Lösung, die aus 85 Gewichtsprozent 4-tert.-Butylbrenzcatechin und 15 Gewichtsprozent Wasser besteht, verwendet. In flüssiger Form ist z. B. das Abfüllen und der Transport leichter durchzuführen. Die Lösungen haben jedoch den Nachteil, daß sie einen hohen Gefrierpunkt von etwa 6 bis 8rC haben und daher während der Lagerung oder des Transportes leicht gefrieren.4-tert-butyibrenzcatechol is used as a polymerization inhibitor for numerous monomers and as an antioxidant for polyolefins, various plastics, lubricants and the like. Although 4-tert-butylpyrocatechol can be used in powder form, it is often used in the form of an aqueous solution consisting of 85 percent by weight of 4-tert-butylpyrocatechol and 15 percent by weight of water for ease of handling. In liquid form, for. B. easier to carry out filling and transport. However, the solutions have the disadvantage that they have a high freezing point of about 6 to 8 r C and therefore easily freeze during storage or transport.

Der Erfindung lag daher die Aufgabe zugrunde, eine homogene, wäßrige 4-tert.-Butylbrenzcatechinlösung mit niedrigem Gefrierpunkt herzustellen, bei der die Polymerisationsinhibitor- und Antioxydations- \virkungdes4-tert.-Butylbrenzcatechinserhalten bleibt.The invention was therefore based on the object of providing a homogeneous, aqueous 4-tert.-butylpyrocatechol solution with a low freezing point, in which the polymerization inhibitor and antioxidant The effect of the 4-tert.-butylpyrocatechol is retained.

Frfindungsgemäß wurde gefunden, daß die Aufgabe dadurch gelöst werden kann, daß man einer wäßrigen 4-tert.-Butylbrenzcatechinlösung einen gesättigten Kohlenwasserstoff als dritten Bestandteil zugibt.In accordance with the invention it was found that the task can be achieved by adding a saturated solution to an aqueous 4-tert-butylpyrocatechol solution Adds hydrocarbon as a third ingredient.

Im allgemeinen sind gesättigte Kohlenwasserstoffe mit Wasser unmischbar bzw. bilden beim Mischen getrennte Phasen, während beim vorliegenden System überraschenderweise eine homogene, stabile Lösung erhalten wird, sofern man bestimmte Mischungsverhältnisse anwendet.In general, saturated hydrocarbons are immiscible with water or form when mixed separate phases, while in the present system, surprisingly, a homogeneous, stable solution is obtained, provided that certain mixing ratios are used.

Gegenstand der Erfindung ist eine homogene wäßrige 4-tert.-Butylbrenzcatechinlösung, bestehend aus 70 bis 90 Gewichtsprozent 4-tert.-Butylbrenzcatechin. j bis 25 Gewichtsprozent Wasser und 5 bis 25 Gewichtsprozent eines gesättigten Kohlenwasserstoffs mit 5 bis 10 Kohlenstoffatomen.The invention relates to a homogeneous aqueous 4-tert-butylpyrocatechol solution, consisting from 70 to 90 percent by weight of 4-tert-butylpyrocatechol. j to 25 percent by weight water and 5 to 25 percent by weight of a saturated hydrocarbon having 5 to 10 carbon atoms.

Geeignete gesättigte Kohlenwasserstoffe sind z. B. n-Pcntan. n-Hcxan. 3-Methylpcntan, 2.3-Dimethyibutan, n-Heptart, 2-MethyIhexan, 3-Äthylpentan, 2,4-Dimethylpentsn, n-Octan, 2-Methylheptan, 2,5-Dimethylhexan, 2,4,4-Trimethylpentan, n-Nonan, n-Decan, Cyclopentan, Cyclohexan, Methylcyclopentan, Methyleyclohexan, Athylcyclopentan, U-Dimethylcyclopentan, l^-Dimethylcyclopentan, Cyclooctan, Äthylcyclohexan, J.B-Dimethylcyclohexan und Paramenlhan. Suitable saturated hydrocarbons are e.g. B. n-pntane. n-Hcxan. 3-methyl pentane, 2,3-dimethyibutane, n-heptart, 2-methylhexane, 3-ethylpentane, 2,4-dimethylpentane, n-octane, 2-methylheptane, 2,5-dimethylhexane, 2,4,4-trimethylpentane, n- Nonane, n-decane, cyclopentane, cyclohexane, methylcyclopentane, methyleyclohexane, ethylcyclopentane, U-dimethylcyclopentane, l ^ -dimethylcyclopentane, cyclooctane, ethylcyclohexane, JB-dimethylcyclohexane and paramenlane.

Zur Herstellung der Lösung werden Wasser, 4-tert.-Butylbrenzcatechin und ein gesättigter Kohlenwasserstoff gründlich miteinander bei Raumtemperatur vermischt. Es kann ein mit einem einfachen Rührer ausgerüstetes Gefäß zum Mischen verwendet werden.To prepare the solution, water, 4-tert-butylpyrocatechol and a saturated hydrocarbon are mixed thoroughly at room temperature mixed. A vessel equipped with a simple stirrer can be used for mixing.

Die Lösungen gemäß der Erfindung haben folgende Vorteile: Eine Alterungsbehandlung, wie sie bei der Herstellung der üblichen ^tert.-Butylbrenzcatechin-p Wassergemische erforderlich ist, ist nicht notwendig; gegenüber den üblichen 4-tert.-Butylbrenzcatechin-Wassergemischen zeigen die Lösungen gemäß der Erfindung bei gleicher 4-tert.-Butylbrenzcatechinkonzentration eine sehr niedrige Viskosität und sind deshalb leichter zu handhaben. Der in den Lösungen gemäß der Erfindung enthaltene gesättigte Kohlenwasserstoff beeinflußt die Polymerisationsreaktinn nicht nachteilig. The solutions according to the invention have the following advantages: an aging treatment, as is necessary in the production of the usual ^ tert-butylpyrocatechol-p water mixtures, is not necessary; Compared to the usual 4-tert-butylpyrocatechol-water mixtures, the solutions according to the invention have a very low viscosity with the same 4-tert.-butylpyrocatechol concentration and are therefore easier to handle. The saturated hydrocarbon contained in the solutions according to the invention does not adversely affect the polymerization reaction.

Die Erfindung wird nachstehend an Hand von Beispielen näher erläutert.The invention is explained in more detail below with the aid of examples.

Die Stabilität der Lösungen wird auf der Basis des Gefrierpunktes bewertet.The stability of the solutions is assessed on the basis of the freezing point.

Beispiel iExample i

Ein Gemisch aus 70 Gewichtsprozent 4-tert.-Butylbrenzcatechin (mit einer P^einheit von 99.5%: bei den folgenden Beispielen wird 4-tert.-[5utylbrenzcatediin gleicher Reinheit verwendet), 9 Gewichtsprozent eines Hexangemisches (aus 65 Gewichtsprozent n-Hexan. 13 Gewichtsprozent 3-Methylpentan. 4 Gewichtsprozent 2-Methylpentan und 18 Gewichtsprozent Methylcyclopenlan)und21 Gewichtsprozent Wasser wurde innig vermischt. Es wurde eine wäßrige Lösung erhalten, die einen Gefrierpunkt von — 2:C hatte. Wenn Hie Lösung ruhig stehengelassen wurde, war sie bei — 10 C mehr als 10 Tage stabil.A mixture of 70 percent by weight of 4-tert-butylpyrocatechol (with a P ^ unit of 99.5%: in the following examples 4-tert .- [5utylpyrocatechol is used in the same purity), 9 percent by weight of a hexane mixture (from 65 percent by weight of n-hexane. 13 percent by weight 3-methylpentane, 4 percent by weight 2-methylpentane and 18 percent by weight methylcyclopenlan) and 21 percent by weight water were intimately mixed. An aqueous solution was obtained which had a freezing point of -2 : C. If the solution was left to stand still, it was stable for more than 10 days at -10 ° C.

Beispiele 2 bis 7Examples 2 to 7

Wasser. 4-tert.-Butylbrenzcatcchin und ein gesättigter Kohlenwasserstoff wurden, wie in der Tabelle angegeben, in der gleichen Weise wie im Beispiel 1 vermischt. Das Mischungsverhältnis der Bestandteile und die Gefrierpunkte der erhaltenen Lösungen sind in der Tabelle angegeben. Alle Lösungen waren bei - 1O0C mehr als 10 Tage stabil, wenn sie ruhig stehengelassen wurden.Water. In the same manner as in Example 1, 4-tert.-butylpyrocatechol and a saturated hydrocarbon were mixed as shown in the table. The mixing ratio of the constituents and the freezing points of the solutions obtained are given in the table. All solutions were at - stable 1O 0 C more than 10 days, if they were allowed to stand still.

Beispiel
Nr.example
No. 4-ierl.-Butyl-
brenzcatechin4-line butyl
catechol Wasserwater Gesättigter KohlenwasserstoffSaturated hydrocarbon ArtArt Gefrierpunktfreezing point (Gewichtsprozent)(Weight percent) (Gewichtsprozent)(Weight percent) (Gewichtsprozent)(Weight percent) CyclohexanCyclohexane CC)CC) 22 7575 12,512.5 12.512.5 2,4,4-Trimethylpentan2,4,4-trimethylpentane -1,7-1.7 33 8080 1414th 66th n-Decann-decane -2-2 44th 8888 66th 66th n-Pentann-pentane 11 55 7272 2323 55 CyclopentanCyclopentane 1,51.5 66th 7272 77th 2121 n-Hexann-hexane _ 2_ 2 77th 7979 55 1616 — 1- 1

Claims (1)

Patentanspruch:Claim: Homogene wäßrige ^tert-Butylbrenzcatechinlösung, bestehend aus 70 bis 90 Gewichtsprozent 4-tert.-Butylbrenzcatechin, 5 bis 25 Gewichtsprozent Wasser und 5 bis 25 Gewichtsprozent eines gesättigten Kohlenwasserstoffs mit 5 bis 10 Kohlenstoffatomen. Homogeneous aqueous ^ tert-butyl catechol solution, consisting of 70 to 90 percent by weight of 4-tert-butylpyrocatechol, 5 to 25 percent by weight Water and 5 to 25 percent by weight of a saturated hydrocarbon having 5 to 10 carbon atoms. IOIO
DE2040151A 1969-08-12 1970-08-12 Homogeneous, aqueous 4-tert-butylpyrocatechnine solution Expired DE2040151C3 (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP44063305A JPS4947632B1 (en) 1969-08-12 1969-08-12

Publications (3)

Publication Number Publication Date
DE2040151A1 DE2040151A1 (en) 1971-03-18
DE2040151B2 true DE2040151B2 (en) 1974-12-05
DE2040151C3 DE2040151C3 (en) 1975-07-31

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US (1) US3656980A (en)
JP (1) JPS4947632B1 (en)
DE (1) DE2040151C3 (en)
GB (1) GB1314390A (en)

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DE69511355T2 (en) 1994-10-28 1999-11-25 Scitex Digital Printing Inc Inkjet imaging with inverse polarity
US7067595B2 (en) * 2003-10-03 2006-06-27 General Electric Company Poly (arylene ether) composition and method
EP2513265A1 (en) * 2009-12-17 2012-10-24 The Lubrizol Corporation Nitrogen-free deposit control fuel additives and one step process for the making thereof
FR3010717B1 (en) * 2013-09-19 2015-11-06 Rhodia Operations COMPOSITION PREVENTING THE POLYMERIZATION OF ETHYLENE-UNATURATED MONOMERS AND ITS DISPOSAL BEFORE POLYMERIZATION

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2114832A (en) * 1936-08-17 1938-04-19 Shell Dev Stabilization of aliphatic mixed ethers
US3405189A (en) * 1966-05-25 1968-10-08 Japanese Geon Co Ltd Method for inhibiting polymerization of isoprene and/or 1, 3-pentadiene

Also Published As

Publication number Publication date
DE2040151C3 (en) 1975-07-31
GB1314390A (en) 1973-04-18
JPS4947632B1 (en) 1974-12-17
US3656980A (en) 1972-04-18
DE2040151A1 (en) 1971-03-18

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Date Code Title Description
C3 Grant after two publication steps (3rd publication)
E77 Valid patent as to the heymanns-index 1977
EHJ Ceased/non-payment of the annual fee